Propionic Acid → 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline

HRID 610470Notes

Reaction equation

HRID 610470 reaction equation
Br[CH:2](Br)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:22]=[CH:21][C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[CH:15][C:14]([C:23]3[CH:28]=CC(C(Br)Br)=[CH:25][CH:24]=3)=[N:13]4)[N:10]=2)=[CH:5][CH:4]=1.[OH-:33].[Na+].[C:35]([OH:39])(=O)[CH2:36][CH3:37]>>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:22]=[CH:21][C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[CH:15][C:14]([C:23]3[CH:28]=[CH:37][C:36]([CH:35]=[O:39])=[CH:25][CH:24]=3)=[N:13]4)[N:10]=2)=[CH:5][CH:4]=1)=[O:33]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 21762037HCID 21762037, compound

Product 1

HCID 217620412,9-bis[p-(formyl)phenyl]-1,10-phenanthroline

Procedure

Compound (3) (2.00 g, 2.96 mmol) and powdered NaOH (0.71 g, 17.7 mmol) were refluxed in propionic acid (15 mL) for 6 h under argon. The propionic acid was evaporated under reduced pressure and replaced with THF (25 mL) and 2M NaOH (5 mL). The solution was stirred for 1 h, and then the THF was evaporated. Water (20 mL) was added and the pH adjusted to ~8 with HCl. The solution was extracted with CH2Cl2 (3×100 mL). Yield 0.92 g (80%). 1H NMR (CDCl3) δ8.38 (s, 2H), 8.64 (d, J=8.4 Hz, 4H), 8.42 (d, J=8.4 Hz, 2H), 8.25 (d, J=8.4 Hz, 2H), 8.13 (d, J=8.4 Hz, 4H), 7.89 (s, 2H).

Workup

  1. customThe propionic acid was evaporated under reduced pressure
  2. customthe THF was evaporated
  3. additionWater (20 mL) was added
  4. extractionThe solution was extracted with CH2Cl2 (3×100 mL)

Sources & evidence

ORD record
ord-1c56bd9942ad4c61a3673d3493e152fa
Source dataset
uspto-grants-1999_12
Patent number
US05998594

Reaction notes

Loading…